The present invention relates to novel compounds suitable for use as dyes for filters, color conversion filters, photographic material dyes, sensitizing dyes, dyes for dying pulp, laser dyes, fluorescent drugs for medical diagnoses and materials for light emitting devices, and light emitting devices using them.
The promising uses of organic electroluminescence (EL) devices as solid light-emission type, low-priced, large-area, full color display devices result in many developments. In general, a light emitting device is composed of a light emitting layer and a pair of counter electrodes between which the light emitting layer intervenes. When an electric field is applied to between both electrodes, electrons are injected from a cathode, and holes are injected from an anode. Further, the electrons and the positive holes are recombined with each other at the light emitting layer to produce an excited state. When this excited state returns to a ground state, energy is released as light, thereby obtaining luminescence.
The conventional light emitting devices have been high in driving voltage, and low in light emitting luminance and light emitting efficiency. Further, they have also been significantly deteriorated in characteristics, so that they have not come in practice. In recent years, a light emitting device in which thin films containing an organic compound having high quantum efficiency and emitting light at a low voltage of 10 V or less are laminated with each other has been reported (Applied Physics Letters, 51, 913 (1987)), and an interest is centered around it. In this device, a metal chelate complex is used as an electron transfer and light emitting material, and laminated with a hole transfer material (amine compound), thereby obtaining green luminescence of high luminance. The luminance reaches thousands of candelas per centimeter square at a voltage of 6-7 V in d.c. However, when considering a practical device, the development of a light emitting device having higher luminance and efficiency has been desired. Further, when considering the utilization thereof as a full color display or a light source, it is practically necessary to give the three primary colors or white. In the above-mentioned device, an aluminum complex of 8-quinolinol (Alq) is used as the light emitting material, so that the light emitting color is green. Accordingly, the development of light emitting materials giving other light emitting colors has been desired. Various light emitting materials emitting colors other than green have hitherto been developed. However, they have the problems of low light emitting luminance and efficiency, and poor durability.
Further, the conventional devices good in color purity and high in light emitting efficiency are ones in which charge transfer materials are doped with fluorescent dyes in slight amounts, and have the problems with regard to the reproducibility of device characteristics from the production point of view, and that the long-term use thereof causes a reduction in luminance and changes in color because of low durability of the dyes. As means for solving the problems, the development of materials having both the charge transfer function and the luminescent function has been desired. However, the materials that have hitherto been developed have the problem that the use of fluorescent dyes at high concentrations leads to a reduction in luminance by association.
On the other hand, organic light emitting devices realizing luminescence of high luminance are devices laminated with organic materials by vapor deposition. The fabrication of the devices by coating is preferred from the viewpoints of simplification of manufacturing processes, processability and enlargement of area. However, the devices fabricated by the conventional coating systems are inferior in light emitting luminance and light emitting efficiency to the devices fabricated by vapor deposition. It has been therefore a great problem to make it possible to emit light of high luminance at high efficiency.
Further, recently, various substances having fluorescence have been used for dyes for filters, color conversion filters, photographic material dyes, sensitizing dyes, dyes for dying pulp, laser dyes, fluorescent drugs for medical diagnoses and materials for light emitting devices have been used, and the demand has increased for them. However, there are not so many compounds high in color purity of blue and strong in fluorescent intensity, so that the development of new materials has been desired.
It is therefore a primary object of the invention to provide materials for light emitting devices and the light emitting devices, in which luminescence of high luminance and efficiency is possible by driving at low voltage, and excellent in stability in repeated use thereof.
A secondary object of the invention is to provide light emitting devices excellent in color purity, and materials for the light emitting devices making it possible.
A third object of the invention is to provide blue light emitting materials excellent in color purity.
A fourth object of the invention is to provide compounds strong in fluorescent intensity and exhibiting blue fluorescent luminescence.
The above-mentioned objects have been attained by the following means:
(1) A material for a light emitting device consisting of a compound represented by the following general formula (IA): 
wherein R11, R12 and R13 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; L1 represents a connecting group; R11 and R12, R11 and L1, and R12 and L1 may each combine with each other to form a ring when possible; R14, R15, R16 and R17 each represents a hydrogen atom or a substituent; and R13 to R17 may each combine with each of R11 to R17 or L1 to form a ring when possible;
(2) A compound represented by the following general formula (IIA): 
wherein R13 represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; L1 represents a connecting group; Q represents an atomic group necessary for forming a 5-, 6- or 7-membered ring with N; R14, R15, R16 and R17 each represents a hydrogen atom or a substituent; and R13, R14, R15, R16 and R17 may each combine with each of R14 to R17, the connecting group L1 or the atomic group Q to form a ring;
(3) A light emitting device comprising a light emitting layer or a plurality of thin organic compound layers containing a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer containing at least one of the compounds represented by general formulas (IA) and (IIA) described in (1) and (2), respectively;
(4) A light emitting device comprising a light emitting layer or a plurality of thin organic compound layers containing a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer in which at least one of the compounds represented by general formulas (IA) and (IIA) described in (1) and (2), respectively, is dispersed in a polymer;
(5) A material for a light emitting device consisting of a compound represented by the following general formula (IB): 
wherein R1 and R2 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Z1 represents an atomic group necessary to form a heterocycle; L represents a connecting group; and X represents O, S, Se, Te or Nxe2x80x94R, wherein R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group;
(6) A material for a light emitting device consisting of a compound represented by the following general formula (IIB): 
wherein R1 and R2 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Z2 represents an atomic group necessary to form an aromatic heterocycle; L represents a connecting group; and X represents O, S, Se, Te or Nxe2x80x94R, wherein R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group;
(7) A material for a light emitting device consisting of a compound represented by the following general formula (III): 
wherein R1 and R2 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Z3 represents an atomic group necessary to form a nitrogen-containing aromatic heterocycle; L represents a connecting group; and X represents O, S, Se, Te or Nxe2x80x94R, wherein R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group;
(8) A material for a light emitting device consisting of a compound represented by the following general formula (IV): 
wherein R1 and R2 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Z4 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; L represents a connecting group; and X represents O, S, Se, Te or Nxe2x80x94R, wherein R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group;
(9) A material for a light emitting device consisting of a compound represented by the following general formula (V): 
wherein R1 and R2 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Z5 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; L represents a connecting group; and X5 represents O, S or Nxe2x80x94R, wherein R represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group;
(10) A material for a light emitting device consisting of a compound represented by the following general formula (VI): 
wherein R1, R2 and R61 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Z6 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; and L represents a connecting group;
(11) A material for a light emitting device consisting of a compound represented by the following general formula (VII): 
wherein R1, R2 and R71 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; Z7 represents an atomic group necessary to form a 6-membered nitrogen-containing aromatic heterocycle; and Ar7 represents arylene or a divalent aromatic heterocycle;
(12) A compound represented by the following general formula (VIII): 
wherein R1, R2 and R81 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; R82, R83 and R84 each represents a hydrogen atom or a substituent, and Ar8 represents arylene or a divalent aromatic heterocycle;
(13) A material for a light emitting device consisting of a compound represented by the following general formula (VIII): 
wherein R1, R2 and R81 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; R82, R83 and R84 each represents a hydrogen atom or a substituent, and Are represents arylene or a divalent aromatic heterocycle;
(14) A compound represented by the following general formula (IX): 
wherein R1, R2 and R91 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; and R92, R93, R94, R95, R96, R97 and R98 each represents a hydrogen atom or a substituent;
(15) A material for a light emitting device consisting of a compound represented by the following general formula (IX): 
wherein R1, R2 and R91 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; and R92, R93, R94, R95, R96, R97 and R98 each represents a hydrogen atom or a substituent;
(16) A compound represented by the following general formula (X): 
wherein R1, R2 and R101 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; and R102, R103, R104, R105, R106 and R107 each represents a hydrogen atom or a substituent;
(17) A material for a light emitting device consisting of a compound represented by the following general formula (X): 
wherein R1, R2 and R101 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; and R102, R103, R104, R105, R106 and R107 each represents a hydrogen atom or a substituent;
(18) A compound represented by the following general formula (XI): 
wherein R1, R2 and R111 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; and R112, R113, R114, R115, R116 and R117 each represents a hydrogen atom or a substituent;
(19) A material for a light emitting device consisting of a compound represented by the following general formula (XI): 
wherein R1, R2 and R111 each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group; and R112, R113, R114, R115, R116 and R117 each represents a hydrogen atom or a substituent;
(20) A light emitting device comprising a light emitting layer or a plurality of thin organic compound layers containing a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer containing at least one of the compounds represented by general formulas (IB), (IIB) and (III) to (XI) described in (5) to (19), respectively; and
(21) A light emitting device comprising a light emitting layer or a plurality of thin organic compound layers containing a light emitting layer formed between a pair of electrodes, wherein at least one layer is a layer in which at least one of the compounds represented by general formulas (IB), (IIB) and (III) to (XI) described in (5) to (19), respectively, is dispersed in a polymer.
The invention will be described in detail below.
First, the compounds of the invention represented by general formula (IA) will be described.
R11 and R12, which may the same or different, each represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. Further, R11 and R12, R11 and L1, and R12 and L1 may each combine with each other to form a ring when possible.
The aliphatic hydrocarbon groups represented by R11 and R12 include a straight-chain, branched or cyclic alkyl group (having preferably from 1 to 30 carbon atoms, more preferably from 1 to 20 carbon atoms, and still more preferably from 1 to 12 carbon atoms, e.g., methyl, ethyl, iso-propyl, n-butyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl or cyclohexyl), an alkenyl group (having preferably from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, and still more preferably from 2 to 12 carbon atoms, e.g., vinyl, allyl, 2-butenyl or 3-pentenyl) and an alkynyl group (having preferably from 2 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, and still more preferably from 2 to 12 carbon atoms, e.g., propargyl or 3-pentynyl). Preferred are the alkyl group and the alkenyl group, and more preferred is methyl, ethyl, propyl, butyl, allyl or a condensed ring formed by bonding of R11 and R12 with L1 (e.g., a julolidine ring).
The aryl groups represented by R11 and R12 are preferably monocyclic or bicyclic aryl groups each having from 6 to 30 carbon atoms (e.g., phenyl and naphthyl). More preferred are phenyl having from 6 to 20 carbon atoms and naphthyl having from 10 to 24 carbon atoms, and still more preferred are phenyl having from 6 to 12 carbon atoms and naphthyl having from 10 to 16 carbon atoms.
The heterocyclic groups represented by R11 and R12 are 3- to 10-membered saturated or unsaturated heterocyclic groups each having at least one of N, O and S atoms. They may be monocyclic or may form condensed rings with other rings.
The heterocyclic groups are preferably 5- to 10-membered aromatic heterocyclic groups each having at least one of nitrogen, oxygen, sulfur and selenium atoms, more preferably 5- or 6-membered aromatic heterocyclic groups, and still more preferably 5- or 6-membered aromatic heterocyclic groups each having an N atom or an S atom.
Specific examples of the heterocyclic groups include pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzthiazole, benzotriazole and tetraazaindene. Preferred are thiophene, triazole, oxazole, pyridine, triazine and quinoline, more preferred are thiophene, pyridine, triazine and quinoline, and still more preferred is thiophene.
The aliphatic hydrocarbon groups, aryl groups and heterocyclic groups represented by R11 and R12 may have substituents. Examples of the substituents include an alkyl group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 12 carbon atoms, and particularly preferably from 1 to 8 carbon atoms, e.g., methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl or cyclohexyl), an alkenyl group (having preferably from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, and particularly preferably from 2 to 8 carbon atoms, e.g., vinyl, allyl, 2-butenyl or 3-pentenyl), an alkynyl group (having preferably from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, and particularly preferably from 2 to 8 carbon atoms, e.g., propargyl or 3-pentynyl), an aryl group (having preferably from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, and particularly preferably from 6 to 12 carbon atoms, e.g., phenyl, p-methylphenyl or naphthyl), an amino group (having preferably from 0 to 20 carbon atoms, more preferably from 0 to 12 carbon atoms, and particularly preferably from 0 to 6 carbon atoms, e.g., amino, methylamino, dimethylamino, diethylamino, diphenylamino or dibenzylamino), an alkoxyl group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 12 carbon atoms, and particularly preferably from 1 to 8 carbon atoms, e.g., methoxy, ethoxy or butoxy), an aryloxy group (having preferably from 6 to 20 carbon atoms, more preferably from 6 to 16 carbon atoms, and particularly preferably from 6 to 12 carbon atoms, e.g., phenyloxy or 2-naphtyloxy), an acyl group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., acetyl, benzoyl, formyl or pivaloyl), an alkoxycarbonyl groups(having preferably from 2 to 20 carbon atoms, more preferably from 2 to 16 carbon atoms, and particularly preferably from 2 to 12 carbon atoms, e.g., methoxycarbonyl or ethoxycarbonyl), an aryloxycarbonyl group (having preferably from 7 to 20 carbon atoms, more preferably from 7 to 16 carbon atoms, and particularly preferably from 7 to 10 carbon atoms, e.g., phenyloxycarbonyl), an acyloxy group (having preferably from 2 to 20 carbon atoms, more preferably from 2 to 16 carbon atoms, and particularly preferably from 2 to 10 carbon atoms, e.g., acetoxy or benzoyloxy), an acylamino group (having preferably from 2 to 20 carbon atoms, more preferably from 2 to 16 carbon atoms, and particularly preferably from 2 to 10 carbon atoms, e.g., acetylamio or benzoylamino), an alkoxycarbonylamino group (having preferably from 2 to 20 carbon atoms, more preferably from 2 to 16 carbon atoms, and particularly preferably from 2 to 12 carbon atoms, e.g., methoxycarbonylamino), an aryloxycarbonylamino group (having preferably from 7 to 20 carbon atoms, more preferably from 7 to 16 carbon atoms, and particularly preferably from 7 to 12 carbon atoms, e.g., phenyloxycarbonylamino), a sulfonylamino group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., methanesulfonylamino or benzenesulfonylamino), a sulfamoyl group (having preferably from 0 to 20 carbon atoms, more preferably from 0 to 16 carbon atoms, and particularly preferably from 0 to 12 carbon atoms, e.g., sulfamoyl, methylsulfamoyl, dimethylsulfamoyl or phenylsulfamoyl), a carbamoyl group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., carbamoyl, methylcarbamoyl, diethylcarbamoyl or phenylcarbamoyl), an alkylthio group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., methylthio or ethylthio), an arylthio group (having preferably from 6 to 20 carbon atoms, more preferably from 6 to 16 carbon atoms, and particularly preferably from 6 to 12 carbon atoms, e.g., phenylthio), a sulfonyl group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., mesyl or tosyl), a sulfinyl group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., methanesulfinyl or benzenesulfinyl), a ureido group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., ureido, methylureido or phenylureido), a phosphoric acid amide group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 16 carbon atoms, and particularly preferably from 1 to 12 carbon atoms, e.g., diethylphosphoric acid amide or phenylphosphoric acid amide), a hydroxyl group, a mercapto group, a halogen atom (e.g., fluorine, chlorine, bromine or iodine), a cyano group, a sulfo group, a carboxyl group, a nitro group, a hydroxamic acid group, a sulfino group, a hydrazine group, an imino group, a heterocyclic group (having preferably from 1 to 30 carbon atoms, and more preferably from 1 to 12 carbon atoms, having a heteroatom, e.g., nitrogen, oxygen or sulfur, and specifically including imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl or benzthiazolyl), and a silyl group (having preferably from 3 to 40 carbon atoms, more preferably from 3 to 30 carbon atoms, and particularly preferably from 3 to 24 carbon atoms, e.g., trimethylsilyl or triphenylsilyl). These substituents may be further substituted. When there are two or more substituents, they may be the same or different. Further, they may combine with each other to form a ring when possible.
R11 and R12 are each preferably a hydrogen atom, an alkyl group, an aryl group and an aromatic heterocyclic group. When the compounds are used as charge transfer materials and concurrently light emitting materials (non-dope type), R11 and R12 are each preferably an aryl group and an aromatic heterocyclic group, and more preferably an aryl group (preferably a monocyclic or bicyclic aryl group having from 6 to 30 carbon atoms, more preferably phenyl or naphthyl having from 6 to 20 carbon atoms, and still more preferably phenyl or naphthyl having from 6 to 12 carbon atoms). When the compounds are used as dope type light emitting materials, R11 and R12 are each preferably a hydrogen atom, an alkyl group or an alkylene group combining with L1 to form a ring, more preferably an alkyl group or an alkylene group combining with L1 to form a ring, and still more preferably an alkyl group having from 1 to 8 carbon toms or an alkylene group combining with L1 to form a 6-membered ring. Particularly preferred are methyl, ethyl and the alkylene group combining with L1 to form a 6-membered ring (e.g., trimethylene and 3,3-dimethyltrimethylene).
R13 represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group. The aliphatic hydrocarbon group represented by R13 is preferably an alkyl group (having preferably from 1 to 20 carbon atoms, more preferably from 1 to 12 carbon atoms, and particularly preferably from 1 to 8 carbon atoms, e.g., methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl or cyclohexyl), an alkenyl group (having preferably from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, and particularly preferably from 2 to 8 carbon atoms, e.g., vinyl, allyl, 2-butenyl or 3-pentenyl), or an alkynyl group (having preferably from 2 to 20 carbon atoms, more preferably from 2 to 12 carbon atoms, and still more preferably from 2 to 8 carbon atoms, e.g., propargyl or 3-pentynyl), and more preferably an alkyl group.
The aryl group represented by R13 has from 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, and particularly preferably from 6 to 12 carbon atoms. Examples thereof include phenyl, p-methylphenyl, m-methylphenyl, o-methylphenyl, p-phenylphenyl, m-phenylphenyl, o-phenylphenyl, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, 2,6-dimethylphenyl, 2,6-diphenylphenyl, 2,4,6-trimethylphenyl, m-trifluoromethylphenyl, pentafluorophenyl, 1-naphthyl and 2-naphthyl.
The heterocyclic group represented by R13 is a monocyclic or condensed heterocyclic group (a heterocyclic group having from 1 to 20 carbon atoms, more preferably from 1 to 12 carbon atoms, and still more preferably from 2 to 10 carbon atoms), and preferably an aromatic heterocyclic group containing at least one of nitrogen, oxygen, sulfur and selenium atoms. Specific examples of the heterocyclic group represented by R13 include pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole, indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxadiazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, acridine, phenanthroline, phenazine, tetrazole, benzimidazole, benzoxazole, benzthiazole, benzotriazole and tetraazaindene. Preferred are furan thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, phthalazine, naphthyridine, quinoxaline, and quinazoline, and more preferred are furan, thiophene, pyridine and quinoline.
The aliphatic hydrocarbon groups, aryl groups and heterocyclic groups group represented by R13 may have substituents. As the substituents, the substituents described above for the groups represented by R11 and R12 can be applied, and preferred substituents are also the same as given therefor.
R13 is preferably an alkyl group, an aryl group or an aromatic heterocyclic group, more preferably an aryl group or an aromatic heterocyclic group, and still more preferably an aryl group or an aromatic azole group.
R14, R15, R16 and R17 each represents a hydrogen atom or a substituent. As the substituents, the substituents described above for R11 and R12 in general formula (IA) can be applied, and preferred examples of R14, R15, R16 and R17 include a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxyl group, an aryloxy group, an acyl group, a halogen atom, a cyano group, a heterocyclic group and a silyl group. More preferred are a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxyl group, an aryloxy group, a halogen atom, a cyano group and an aromatic heterocyclic group, still more preferred are a hydrogen atom, an alkyl group, an aryl group and an aromatic heterocyclic group, and particularly preferred is a hydrogen atom. Further, the substituents may combine with each other, or the substituent may combine with the connecting group L1 to form a ring when possible.
L1 represents a connecting group. The connecting group represented by L1 is preferably a connecting group formed by a single bond, C, N, O, S, Se, Te, Si or Ge, more preferably a group comprising a single bond, alkylene, alkenylene, alkynylene, arylene, a divalent heterocycle (preferably an aromatic heterocycle, and more preferably an aromatic heterocycle formed by an azole, thiophene or furan ring) or a combination thereof with N, and still more preferably a group comprising arylene, a divalent aromatic heterocycle or a combination thereof with N. Yet still more preferred is a group comprising a phenylene group, a thenylene group or a combination thereof with N, and particularly preferred is a phenylene group. Further, L1 may combine with R11 to R17 to form a ring.
Specific examples of the connecting groups represented by L1 include the following groups as well as a single bond. 
The connecting groups represented by L1 may have substituents. As the substituents, for example, the substituents described above for the groups represented by R11 and R12 can be applied. Preferred examples of the substituents for L1 include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxyl group, an aryloxy group, an acyl group, a halogen atom, a cyano group, a heterocyclic group and a silyl group. More preferred are an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxyl group, an aryloxy group, a halogen atom, a cyano group and an aromatic heterocyclic group, and still more preferred are an alkyl group, an aryl group and an aromatic heterocyclic group.
Of the compounds represented by general formula (IA), compounds represented by the following general formula (IIA) are preferred. 
R13, R14, R15, R16, R17 and L1 each has the same meaning as given for general formula (IA), and each preferred range is also the same as given therefor.
Q represents an atomic group necessary to form a 5-, 6- or 7-membered nitrogen-containing heterocycle by combining with N.
The 5- to 7-membered nitrogen-containing heterocycles formed by Q and N include a pyrrole ring, an azepine ring, a piperidine ring, a pyrrolidine ring, a piperazine ring, a morpholine ring, a thiomorpholine ring and a hexamethyleneimine ring, and preferred are a pyrrole ring and an azepine ring.
The 5- to 7-membered nitrogen-containing heterocycles formed by Q and N may further combine with other rings to form condensed rings, and may also have substituents. The condensed rings include, for example, a benzene ring, a thiophene ring, a pyrrole ring, a furan ring, a selenophene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an imidazole ring, an oxazole ring and a thiazole ring. Preferred are a benzene ring, a thiophene ring, a pyridine ring and a pyrazine ring, more preferred are a benzene ring and a thiophene ring, and particularly preferred is a benzene ring. As the substituents, for example, the substituents described above for the groups represented by R11 and R12 can be applied. Preferred examples of the substituents for Q include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an amino group, an alkoxyl group, an aryloxy group, an acyl group, a alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a sulfonyl group, a halogen atom, a cyano group and a heterocyclic group. More preferred are an alkyl group, an alkenyl group, an aryl group, an alkoxyl group, an aryloxy group, a halogen atom, a cyano group and a heterocyclic group, still more preferred are an alkyl group, an aryl group, an alkoxyl group, an aryloxy group and an aromatic heterocyclic group, and particularly preferred are an alkyl group, an aryl group, an alkoxyl group and an aromatic heterocyclic group.
Specific examples of the 5- to 7-membered rings formed by Q and N include, for example, the following. 
The compounds represented by general formulas (IA) and (IIA) may be either low molecular weight compounds, or high molecular weight compounds in which residues are connected to main chains of polymers (the weight-average molecular weight of the compounds is preferably from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and still more preferably from 10,000 to 1,000,000) or high molecular weight compounds having the compounds of the invention as main chains (the weight-average molecular weight of the compounds is preferably from 1,000 to 5,000,000, more preferably from 5,000 to 2,000,000, and still more preferably from 10,000 to 1,000,000). In the case of the high molecular weight compounds, they may be either homopolymers or copolymers with other polymers. In the case of the copolymers, they may be either random copolymers or block copolymers. The compounds used in the invention are preferably the low molecular weight compounds.
Specific examples of the compounds of the invention represented by general formula (IA) are shown below, but it is to be understood that the invention is not limited thereto. 
The above-mentioned compounds may be their tautomers.